James “Jim” Kelly, born in Williamson County, Texas, was the son of manumitted slaves, “Uncle Amos” and “Aunt Phoebe” Kelly, who had belonged to the Olive clan, a family of powerful Texas cattlemen. After 1865 Kelly worked for Isom Prentice (Print) Olive, a former Confederate soldier, becoming a trail boss and gunman for the Olive ranch. Kelly functioned as a regulator whenever the Olives believed their enemies deserved extralegal justice. As a grown man, Kelly was slim and ruggedly handsome, standing six feet six inches tall.
The Olive ranch dealt with cattle rustlers, often inflicting swift and punitive justice on them. Print Olive, his brothers Thomas, Ira and Bob and Jim Kelly often shot thieves on the spot. Soon they became known and feared as a “gun outfit.” Kelly’s gun-slinging skills made him the top enforcer or “regulator” for the Olives.
When Texas to Kansas cattle drives began in 1866, Print Olive and a trail crew that included Kelly drove several thousand head to Sedalia, Kansas. Three years later in 1869 Olive and Kelly took two thousand cattle to Fort Kearny, Nebraska. Olive and Kelly returned to Texas with $50,000. On the 1872 drive to Abilene, Kansas, Print Olive, after selling three thousand cattle and making a $45,000 profit, headed for a poker game in an Abilene saloon where he got into an altercation with a gambler. Kelly’s fast gun saved Olive’s life.
In 1878, Print Olive moved his cattle operation north to Nebraska. Kelly and other cowboys employed by Olive drove fifteen thousand head of cattle to Custer County, Nebraska. To police the range against rustlers and homesteaders, ranchers formed the Custer County Livestock Association, electing Print as its first president with Jim Kelly as the association’s chief enforcer.
Later that year problems developed between the Olive brothers and two homesteaders whom they charged with killing their cattle. After capturing the men, Print Oliver ordered them hanged. Olive, Jim Kelly, and others were later arrested. Although charges were dismissed against Kelly and the other men, Print Olive went to prison.
James Kelly spent his last years in Ansley, Nebraska, dying in February 1912, at seventy-three.